ChemicalBook--->CAS DataBase List--->13726-67-5

13726-67-5

13726-67-5 Structure

13726-67-5 Structure
IdentificationMore
[Name]

Boc-Asp-OH
[CAS]

13726-67-5
[Synonyms]

BOC-ASPARTIC ACID
BOC-ASP-OH
BOC-L-ASPARTIC ACID
BOC-L-ASPARTIC ACID-OH
BOC-L-ASP-OH
N-ALPHA-T-BOC-L-ASPARTIC ACID
N-ALPHA-T-BUTOXYCARBONYL-N-ASPARTIC ACID
N-BOC-L-ASPARTIC ACID
N-T-BUTOXYCARBONYL-L-ASPATIC ACID
N-(TERT-BUTOXYCARBONYL)-L-ASPARTIC ACID
N-TERT-BUTYLOXYCARBONYL-L-ASPARTIC ACID
N-T-BOC-L-ASPARTIC ACID CRYSTALLINE
BOC-L-Aspatic
N-BOC-1-ASPARTICACID
BOC-ASP
BOC-L-ASPARTICACID(BOC-L-ASP-OH)
Boc-L-Aspatic Acid
BOC-L-ASP
N-alpha-t-Butyloxycarbonyl-L-aspartic acid
N-Boc-L-aspartic acid, 98+%
[EINECS(EC#)]

237-294-7
[Molecular Formula]

C9H15NO6
[MDL Number]

MFCD00037279
[Molecular Weight]

233.22
[MOL File]

13726-67-5.mol
Chemical PropertiesBack Directory
[Appearance]

white to off-white crystalline powder
[Melting point ]

116-118 °C(lit.)
[alpha ]

-6 º (c=1, MeOH)
[Boiling point ]

375.46°C (rough estimate)
[density ]

1.3397 (rough estimate)
[refractive index ]

1.4640 (estimate)
[storage temp. ]

Store at RT.
[form ]

Crystalline Powder
[pka]

3.77±0.23(Predicted)
[color ]

White to off-white
[Optical Rotation]

[α]20/D 6.0°, c = 1 in methanol
[BRN ]

1913973
[Major Application]

peptide synthesis
[InChI]

1S/C9H15NO6/c1-9(2,3)16-8(15)10-5(7(13)14)4-6(11)12/h5H,4H2,1-3H3,(H,10,15)(H,11,12)(H,13,14)/t5-/m0/s1
[InChIKey]

KAJBMCZQVSQJDE-YFKPBYRVSA-N
[SMILES]

CC(C)(C)OC(=O)N[C@@H](CC(O)=O)C(O)=O
[CAS DataBase Reference]

13726-67-5(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[HS Code ]

29225090
[Storage Class]

11 - Combustible Solids
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Boc-Asp-OH(13726-67-5).msds
Hazard InformationBack Directory
[Chemical Properties]

white to off-white crystalline powder
[Uses]

N-Boc-L-aspartic acid is an N-Boc-protected form of L-Aspartic acid (A790024). L-Aspartic acid is a nonessential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.
[Definition]

ChEBI: Nalpha-(tert-butoxycarbonyl)-l-aspartic acid is an aspartic acid derivative.
[reaction suitability]

reaction type: Boc solid-phase peptide synthesis
[Synthesis]

L-Aspartic acid

56-84-8

Di-tert-butyl dicarbonate

24424-99-5

Boc-Asp-OH

13726-67-5

GENERAL STEPS: In a 500 mL single-necked round-bottomed flask, L-aspartic acid (4 g, 30 mmol), 1,4-dioxane (120 mL) and deionized water (60 mL) were mixed to form a heterogeneous solution. Under continuous stirring, 1 M aqueous sodium hydroxide solution was added dropwise until the solution became homogeneous and clarified, indicating complete dissolution of L-aspartic acid. Subsequently, the reaction mixture was cooled in an ice bath and di-tert-butyl dicarbonate (7.2 g, 33 mmol) dissolved in 1,4-dioxane (20 mL) was added slowly and dropwise. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was partially evaporated using a rotary evaporator until the final volume was about 30 mL. ethyl acetate (20 mL) was then added and the aqueous layer was acidified to pH 2 with aqueous potassium bisulfate under ice-bath cooling conditions. the mixture was transferred to a partitioning funnel, and the product was extracted with ethyl acetate (3 aliquots at a time). The organic layers were combined and dried with anhydrous sodium sulfate. Subsequently, the solvent was evaporated using a rotary evaporator and further dried under vacuum overnight to give BOC-L-aspartic acid as a white solid (6 g, 85% yield).1H NMR (600 MHz, DMSO-d6) data: δ 1.38 (s, 9H), 2.51-2.55 (m, 1H), 2.65-2.69 (m, 1H). 4.24-4.28 (m, 1H), 7.05-7.07 (d, 1H, J = 12 Hz), 12.5 (s, 2H).

[References]

[1] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16084 - 16097
[2] Patent: US2017/168042, 2017, A1. Location in patent: Paragraph 0203-0204
[3] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722
[4] Patent: EP1647283, 2006, A1. Location in patent: Page/Page column 5
[5] Chemistry Letters, 1988, # 10, p. 1643 - 1646
Spectrum DetailBack Directory
[Spectrum Detail]

Boc-Asp-OH(13726-67-5)MS
Boc-Asp-OH(13726-67-5)1HNMR
Boc-Asp-OH(13726-67-5)IR1
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

N-Boc-L-aspartic acid, 98+%(13726-67-5)
[Sigma Aldrich]

13726-67-5(sigmaaldrich)
[TCI AMERICA]

N-(tert-Butoxycarbonyl)-L-aspartic Acid,>97.0%(GC)(T)(13726-67-5)
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